1. Nomenclature III
Functional Groups

2. These slides are best when downloaded and run on powerpoint due to the animations.

3. Simple Names Base name: The name appears at the end of the name
Suffix name: The name appears at the end of the name
Prefix name: The name appears before the base name
Some sound better than others
If we can unambiguously draw a structure from your name,
Then you will get a majority of the credit

4. Simple Names: Alcohol Base name: alcohol Suffix name: -anol or -ol
R-OH where R = any sp3 C
Suffix name: -anol or -ol
To be considered an alcohol, the carbon attached to the OH should be sp3 hybridized.
Prefix name: hydroxy-
ethyl alcohol
ethanol
hydroxyethane
PREFERRED
tert-butyl alcohol
t-butyl alcohol
2-methyl-2-propanol
2-methyl-2-propyl alcohol
2-hydroxy-2-methylpropane
PREFERRED
4,7-dihydroxy-3-methyloctane
2,5-dihydroxy-6-methyloctane
6-methyl-2,5-octanediol
PREFERRED

5. If the C is sp2, then ...
enols are typically very unstable and are short lived.
There are a few examples of stable enols, but we will not talk about them.
If it is a simple alkene, the functional group is called an enol.
You will not be required to name enols.
If it is a benzene ring, the functional group is called an phenol.
Unlike enols, phenols are very stable.
phenol
4-bromophenol
3-chlorophenol
You may be required to name phenols.

6. Simple Names: Amine Base name: amine Prefix name: amino-
where R = any sp3 C or H
Prefix name: amino-
To be considered an amine, the carbon attached to the N should be sp3 hybridized.
NH3
ammonia
ethyl amine
aminoethane
PREFERRED
N-isobutyl-methylamine
N-methyl-2-methylpropylamine
PREFERRED
N prefix is used to show group
is attached to the nitrogen
1,3-diaminopropane
benzylamine
N,N-diisopropylethylamine

7. If the C is sp2, then ...
enamines are more stable than enols
If it is a simple alkene, the functional group is called an enamine.
You will not be required to name enamines.
If it is a benzene ring, the functional group is called an aniline.
anilines are very stable
2-aminophenol
2-hydroxyaniline
You may be required to name anilines.

8. Simple Names: Ether Base name: ether Prefix name: -oxy-
R-O-R where R = any C
Name one side, than the other followed by ether.
Prefix name: -oxy-
This molecule is commonly referred to as ether.
ethyl methyl ether
methoxyethane
ethoxymethane
PREFERRED
diethyl ether
ethyl ether
ethoxyethane
PREFERRED
1,2-dipropoxypropane
4,7-dioxa-5-methyldecane
PREFERRED
ethyl phenyl ether
phenoxyethane
ethoxybenzene
PREFERRED
ADVANCED NAME: You will not be responsible for this name.

9. Simple Names: Carbonyls
is a carbonyl.
There are many functional groups that contain carbonyls:
aldehydes, ketones, carboxylic acids, esters, amides

10. Simple Names: Aldehyde
Base name: aldehyde
where R = any C or H
Suffix name: -anal
methanal
formaldehyde
Common
Technically correct
ethanal
acetaldehyde
Common
Technically correct
butanal
butyraldehyde
PREFERRED
3-methoxybenzaldehyde
PREFERRED

11. Simple Names: Ketone Base name: ketone Suffix name: -one
where R = any C
propanone
dimethyl ketone
acetone
Common
Technically correct
2-pentanone
methyl propyl ketone
PREFERRED
2,5-heptanedione
PREFERRED
3-methyl-2,4-pentanedione
PREFERRED

12. Simple Names: Carboxylic acid
Suffix name: -oic acid
where R = any C or H
methanoic acid
formic acid
Common
Technically correct
ethanoic acid
acetic acid
Common
Technically correct
2-hydroxybenzoic acid
salicylic acid OK
Common
(Do not need to know)
phenylacetic acid
PREFERRED

13. Simple Names: Ester Suffix name: -oate or -ate where R = any C or H
-yl side
where R = any C or H
where R’ = any C
-ate side
isopropyl formate
methylethyl methanate
Common
ethyl acetate
ethyl ethanoate
Common
phenyl pentanoate
butyl benzoate

14. Functional Groups: You need to know these, but not name them yet…
amide
nitrile
thioether
nitro
sulfonic acid
thiol

15. Exam Level Questions: Draw the following: ethyl propionate
3-aminobutanal
2,2-dimethylhexanoic acid
Z-4,4-dimethoxy-2-heptene
triethylamine
trifluoroacetic acid